Just beginning to plan need some advice

You have a good start with knowing you want to stay four nights in each place, but "south" is pretty vague. Are you thinking of flying home from Rome or ???
The DK travel guide to Liguria is one I found fairly comprehensive. It is perfect for train travel, as the train line goes along the coast--all you have to do is pick a place.

The Cinque Terre is south of Milan, so You could make a round trip by train.
Milan's MXP airport >Lake Como >Milano Centrale >Monterosso (Cinque Terre) >Florence > Milano Centrale > MXP > Home.

Sorry about the “south” without being clear. We are thinking of the Cinque cities indeed. And I prefer not to go further South than Florence.

Also excellent point about flying. No idea where we should fly in and out but any advice would be great.

This is why I love the forum. Y’all think about the stuff I haven’t thought about but need to!!

You could fly into Milan, head to lakes, come back through Milan and take train to whichever Cinque Terre village you choose, then finish in Tuscany and fly out of Pisa or Florence. Lucca is really popular but you have literally hundreds of options.

Love the 4, 4, 4 plan.

In general I’d avoid CT in the summer but early June sounds like a good way to see it before the heat or crowds become overbearing. This is especially effective for your no rushing around plan. I’d stay somewhere with a pretty view that gives you a little insulation from the hubbub.

Bergamo and Verona are lovely but most would say there’s not enough to do for 4 days. I’d say you could fill a day or two fully with historical sites and then have plenty of time to stroll, dine and take day trips.

If you don't want to go as far south as Rome, and you are set on the CT, then fly R/T Milan. Milan is a large international airport with lots of destinations and generally good prices. Flying from a smaller regional airport could be more expensive and entail more connections.

With that, the best itinerary would be straight to Como from Milan airport, then your 2nd stop, ending in the CT and a late afternoon train to Milan for your last night before flying home.

Consider staying in Bologna. From there you can day trip by train to a number of interesting towns, including Florence. Others are Padua, Ferrara, Modena, even Verona.

Excellent advice. Thank you all so much. I’ll start planning the trip flying in and out of Milan. No doubt someone in our group will throw a monkey wrench into it (hubby now wondering if we should go back to Murren, Switzerland to start trip) but it’s a start.
😂😂😂😂

If you fly out of Charlotte, look at flying into Genova. 1H09m train to Monterosso. Then train to Florence, train to Lake Como. Fly home from Milan.

You need to consider the time of your departing flight. The airlines normally want you there around three hours before a flight to the USA. This is perfectly possible using trains from central Milan. The trains from Milano Cadorna take 37 minutes and run every 30 minutes from 04.57. The trains on the other train line from Milano Centrale and Milano Porta Garibaldi also run every 30 minutes, starting 05.25 and 05.35 and taking 51 minutes and 41 minutes respectively.

https://www.malpensaexpress.it/en/

So if there is an early morning departure you would want to spend the previous night at a Malpensa hotel, not needing to arrive until dinner time; in that instance you would stay in Milan first. The Villa Malpensa is 8 minutes to the airport, is comfortable and has an excellent restaurant.

Don’t skip Florence! It is an amazing city! Also day trip from there to other Tuscan cities examples might be Sienna, Lucca or the Chiantia area for a little wine tasting.

Great!! I’ll be liking into this and I ordered some RS books on Italy as well. Thank you!!

Are you considering Venice?

No, not Venice. I think the idea is to spend more time in a smaller section instead of trying to see it all. Really take it slow to enjoy the region.

In 2021, we went to Lake Como, Verona, and Venice for a total of 12 nights. We flew into Milan and out of Venice.

I just saw you said no Venice but you might consider Verona.

Why don't you buy RS's book or other books? That why they exist to provide advice.

Any kind of advice we can offer would be better if it's more relevant to your actual needs and preferences. There are different routes for foodies, or photographers, wine lovers, culture lovers, history lovers, etc.

The distance on a map is not necessarily proportional to travel time. For example, Milan to Cinque Terra might take 3 hours, but I think you can get from Milan to Rome in that same time. The difference is high speed trains with few stops, versus slower trains with many stops, and a view changes of train.

After numerous trips to Italy to over 50 locations, I have come to the conclusion that most of the most famous places are over-rated and over-crowded with tourists.

A place like Florence or Rome - make sure you have reservations to museums or parks days or weeks in advance of arrival.

Cinque Terra has some nice views - but not that many vantage points - so all the photos look the same essentially. And there is not much to do other than walk around a bit.

There is also Bergamo, Sermione, Treviso, Stresa, Bolzano, Trento, Torino, Alba and Asti, Portafino, etc - just in that northern tier alone.

Yes, I did order some RS books already. I will use them to help plan as well as this forum.
Thanks!